(S)-(4-(3-Cyclohexyl-4-(pyrrolidin-3-yloxy)benzoyl)piperazin-1-yl)(3-fluoro-5-(piperazin-1-yl)phenyl)methanone didihydrochloride

ID: ALA3819506

PubChem CID: 127052189

Max Phase: Preclinical

Molecular Formula: C32H44Cl2FN5O3

Molecular Weight: 563.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.Cl.O=C(c1cc(F)cc(N2CCNCC2)c1)N1CCN(C(=O)c2ccc(O[C@H]3CCNC3)c(C3CCCCC3)c2)CC1

Standard InChI:  InChI=1S/C32H42FN5O3.2ClH/c33-26-18-25(19-27(21-26)36-12-10-34-11-13-36)32(40)38-16-14-37(15-17-38)31(39)24-6-7-30(41-28-8-9-35-22-28)29(20-24)23-4-2-1-3-5-23;;/h6-7,18-21,23,28,34-35H,1-5,8-17,22H2;2*1H/t28-;;/m0../s1

Standard InChI Key:  KTKFYLCCPOUIDU-ZXVJYWQYSA-N

Molfile:  

     RDKit          2D

 43 46  0  0  0  0  0  0  0  0999 V2000
    6.1607    1.3263    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0351    3.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039    3.7494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031   -3.0008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039   -3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4469   -5.2297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9152   -5.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6607   -4.2349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532   -3.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3092    5.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6108    5.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9073    5.2404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9021    3.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6005    2.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2112    5.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5072    5.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2174    7.1836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8115    5.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1053    5.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0949    3.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7907    2.9679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4969    3.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7824    1.7679    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4102    5.9502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4230    7.4502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7284    8.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0210    7.4281    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0082    5.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7029    5.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991   -0.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1969   -1.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1945   -3.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8943   -3.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5964   -3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6607    1.3263    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  4  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 12 11  1  6
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
 10 17  1  0
 10 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 23  1  0
 28 30  1  0
 31 32  1  0
 31 36  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 26 31  1  0
 37 38  1  0
 37 42  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
  6 37  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 563.72

Molecular Weight (Monoisotopic): 563.3272

AlogP: 3.62

#Rotatable Bonds: 6

Polar Surface Area: 77.15

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 10.31

CX LogP: 3.46

CX LogD: -0.72

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.56

Np Likeness Score: -0.86

References

1. Wisniewski JA, Yin J, Teuscher KB, Zhang M, Ji H..  (2016)  Structure-Based Design of 1,4-Dibenzoylpiperazines as β-Catenin/B-Cell Lymphoma 9 Protein-Protein Interaction Inhibitors.,  7  (5): [PMID:27190602] [10.1021/acsmedchemlett.5b00284]

2. Teuscher KB, Zhang M, Ji H..  (2017)  A Versatile Method to Determine the Cellular Bioavailability of Small-Molecule Inhibitors.,  60  (1): [PMID:27935314] [10.1021/acs.jmedchem.6b00923]

Source

Source(1):

• Scientific Literature